Cummings is a Cicero, N.Y. native and graduated from Siena College in New York. Cummings set the Siena College single-season strikeout record with 91 in 2016. Cummings his finished college career with 169 strikeouts in 195.1 innings. He began 2017 with the Southern Maryland Blue Crabs and pitched in the California Winter League last year for the league champion New York Colonials. Cummings went 4-1 in 13 games played and 19 1/3 innings pitched while picking up four saves, 26 strikeouts, two walks and finished with a 1.08 ERA. In 2017 with the Otters, Cummings was 4-2 with seven saves, 58 strikeouts and a 1.22 ERA, earning him the Frontier League's Rookie of the Year Award.